Chicago

Chicago Hotels with Rooftop Pools

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8 Chicago Hotels with Rooftop Pools Found for You

Choose your travel dates to see the latest prices and deals.
Most Booked
Lowest price
Closest to downtown
Highest Rated
99+

Best Western River North Hotel

Hotel near River North,Chicago
"The Best Western River North Hotel is a practical choice for exploring Chicago, thanks to its excellent location near the Magnificent Mile. The rooms are clean and functional, providing a comfortable base for a short stay. One of the highlights is the rooftop deck, which offers great views of the city skyline. Having an indoor pool and on-site parking is also a major convenience for this downtown area. It offers reliable value for those who want to be close to the action without the luxury hotel price tag. And we had an amazing walk to union train station"
Good
57 reviews
7.9/10
1 night
From SAR 442
Check availability
99+

Holiday Inn & Suites CHICAGO-DOWNTOWN by IHG

Hotels in Chicago
Featured facilities: Pool, Gym, Laundry service (on-site)
Very Good
41 reviews
8.9/10
1 night
From SAR 461
Check availability
99+

DoubleTree by Hilton Chicago Magnificent Mile

Hotel near Streeterville,Chicago
"great safe location , the rooftop pool with skyline views and grab and go with food and drinks was awesome."
Very Good
283 reviews
8.8/10
1 night
From SAR 698
Check availability
78

Hilton Grand Vacations Club Chicago Magnificent Mile

Hotel near Streeterville,Chicago
Featured facilities: Pool, Bar, Gym
Great
101 reviews
9.0/10
1 night
From SAR 1,041
Check availability
99+

Viceroy Chicago

Hotel near River North,Chicago
Featured facilities: Pool, Sunbathing area, Bar
Great
108 reviews
9.0/10
Check availability
99+

Hyatt House Chicago West Loop

Hotel near West Loop,Chicago
"During the epidemic, breakfast was filled with bread, fruit and coffee in kraft paper bags, but check in and check out were quite fast. The parking lot is very small. It is not easy to see $50 a night at night. The overall environment of the hotel is very good, the facilities are very new, the decoration is also very good, there is a swimming pool and a gym, the price is good, it is recommended!"
Very Good
104 reviews
8.9/10
1 night
From SAR 1,100
Check availability
96

The Hoxton, Chicago

Hotel near West Loop,Chicago
Featured facilities: Pool, Bar, Gym
Great
101 reviews
9.0/10
Check availability
99+

The Robey, Chicago, a Member of Design Hotels

Hotel near Wicker Park,Chicago
Featured facilities: Pool, Bar, Massage room
Great
101 reviews
9.1/10
1 night
From SAR 842
Check availability
See More Hotels with Rooftop Pools in Chicago

What's new in Chicago

Updated on October 26, 2026

Navy Pier Winter Fireworks Show

The spectacular, free, and award-winning fireworks display at Navy Pier returns for winter 2026! Experience the magic of winter fireworks every Saturday night at 8 p.m.! Enjoy a comfortable evening on the pier, watching the dazzling fireworks and breathtaking city skyline views!

Navy Pier’s Winter WonderFest

Winter Wonder Festival at Navy Pier — Chicago Holiday Experience Winter Wonder Festival: Experience magical holiday fun at Chicago's Navy Pier with a stunning 42-foot Christmas tree, thrilling rides (Cliff Drift, Zero Gravity, bumper cars), ice skating, and seasonal attractions for all ages.

The Wintrust Magnificent Mile Lights Festival

Wintrust Grand Parade of Lights — 35th Annual Wintrust Grand Parade of Lights: America's largest nighttime parade on November 21st featuring Mickey and Minnie Mouse, Disney floats, marching bands, Santa, the Wintrust Fireworks Show, and millions of lights along North Michigan Avenue!

Frequently Asked Questions

What is the average price of a hotel in Chicago for this weekend?

According to the latest 12-month data from Trip.com, the average price for a 3-star hotel in Chicago this weekend is SAR 1,050 per night. For a 4-star hotel, the average cost is SAR 1,411 per night. If you're looking for a luxury experience, 5-star hotels in Chicago this weekend typically cost SAR 3,788 per night.

How much do hotels in Chicago cost per night during weekdays?

Based on the latest 12-month data from Trip.com, the average price for a 3-star hotel in Chicago during weekdays is SAR 928 per night. For a 4-star hotel, you can expect to pay around SAR 1,291 per night. If you're looking for a luxury stay, 5-star hotels in Chicago generally cost SAR 3,475 per night on weekdays.

What are the best places to stay in Chicago?

Some of the best places to stay in Chicago are near popular attractions like Millennium Park, Willis Tower and Magnificent Mile, offering easy access to key sights and amenities.

What are the top hotels in Chicago near Millennium Park?

Some of the top hotels in Chicago near Millennium Park include The Palmer House Hilton (from SAR 638), Swissotel Chicago (from SAR 735) and L7 Chicago (from SAR 552), all offering easy access to Millennium Park, making them ideal for visitors looking to explore the area.

What are the best hotels with a spa in Chicago?

Plan a peaceful trip? Spa can be a wonderful experience when traveling. Warwick Allerton Chicago (from SAR 340), HI Chicago Hostel (from SAR 160) and Best Western Grant Park Hotel (from SAR 488) provide highly rated spa services.

What hotels in Chicago provide airport transfer services?

Not familiar with Chicago? Holiday Inn CHICAGO O'HARE AREA by IHG (from SAR 460), Renaissance Chicago O'Hare Suites Hotel (from SAR 537) and SpringHill Suites Chicago O'Hare (from SAR 436) are popular hotels with airport shuttle.

What hotels in Chicago provide swimming pools?

Best Western River North Hotel (from SAR 441), Hilton Garden Inn Chicago Downtown/Magnificent Mile (from SAR 497) and Embassy Suites by Hilton Chicago Downtown River North (from SAR 617) are hotels with swimming pools. Book now and enjoy your swimming pool!

Which hotels in Chicago have the best breakfast?

Warwick Allerton Chicago (from SAR 340),Hilton Chicago O'Hare Airport (from SAR 724) and Swissotel Chicago (from SAR 735) offer high-quality breakfast. Enjoy your wonderful journey with delicious breakfast!

What hotel deals are available in Chicago?

Trip.com offers multiple promotions and discounts all year round for both new users and loyal customers . Please check the promotions page to see what promotions are available now on Trip.com.